
Holiday rentals in Pleasantville
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Top-rated holiday rentals in Pleasantville
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RARE Spacious Treehouse & Sauna Near Des Moines
Come home to luxury in nature in this spacious, double king-bed treehouse and sleep among the stars. Expansive views of rolling hills greet you as you sip your pour-over coffee on the wrap around balcony twenty feet above ground. Rain? No problem. Tuck away on the three-season screened-in porch to watch the iconic Iowa pink sunsets. Built with special touches including stained glass and intricate woodwork, this treehouse boasts warmth throughout and is sure to be a once-in-a-lifetime get-away.
4.99 out of 5 average rating, 104 reviews
Historic Home on 4 Acres - Hot Tub, Pool, Tiki Bar
Our 1948 vacation home is on 4 acres & boasts 3 bedrooms, 3 full baths, 2 half baths, Bridal Suite (4th bedroom), 70s TV/Game Room, Tiki Bar, & Children's Playroom. Outside we have a pool (guaranteed to be open 5/26 - 9/5) & hot tub (year round). Located 15min away from Downtown DSM & a mile away from a grocery store/restaurants. Up to 2 dogs allowed for an additional fee. ***Events/photo shoots are allowed with written permission only and will be an added fee. No events larger than 25 total.***
4.97 out of 5 average rating, 212 reviews
The Hen House
The wonderfully remodeled home based on 55 acres overlooking mature trees and a large pond. The house has 3 bedrooms and 1 1/2 baths. Laundry is available to use as well. Kitchen is fully stocked for your cooking enjoyment and a gas grill is offered as well to use. This house is perfect for families, small groups, or business trips. Situated just 20 minutes from Des Moines airport, and 25 minutes from downtown Des Moines, you will be able to experience the quiet and beautiful scenery to enjoy.
5.0 out of 5 average rating, 207 reviews
Private lake, lodge & 23 acres south of Des Moines
Amazing, secluded 23 acres of property highlighted with a 6 BR lodge and your own PRIVATE lake. For the bike enthusiast, the famous 17 mile Great Western bike trail is located right at the driveway. For the kids or kid-at-heart, enjoy numerous activities & games: - basketball court - sand VB court - 6 kayaks - 2 ping pong tables - billiards table - air hockey - 2 foosball tables - numerous board & card games - ladder ball, bag toss Located <15 miles south of Des Moines/Jordan Creek Mall.
4.95 out of 5 average rating, 101 reviews
This is the best Des Moines has to offer!
Welcome to a beautiful 3 story townhome in the heart of Des Moines. If an upscale modern home with an incredible view is your thing, you will be in heaven. Inside you’ll find a clean, bright and well decorated home with all the amenities you'll need to kick back, relax and enjoy your stay. Minutes from shopping, dining and nightlife. The bike trail is across the street where you can ride to Gray’s Lake or stroll to downtown DSM and enjoy the Farmer's Market, Civic Center and Principal Park.
4.94 out of 5 average rating, 153 reviews
Charming Garden Suite at PineRidge Rose Farm
Experience the quiet beauty of the Iowa countryside at PineRidge Roses. Whether you’re here for the high-octane excitement of the Knoxville Raceway or the Dutch charm of Pella, our suite offers a fragrant, peaceful home base. As a guest, you’re staying on a developing a flower farm. While we are still growing and building our floral dreams, you might see active farm working during the day. The reward is a fresh, hand-picked bouquet waiting in your suite to brighten every morning of your stay.
4.97 out of 5 average rating, 94 reviews
Cozy Loft South of Pleasantville
Escape to the countryside with a stay in our charming lofted studio, attached to our family home and nestled on a peaceful farm just 10 minutes from Pleasantville, Iowa. This cozy retreat offers a private studio-style space perfect for a quiet getaway We’re just 15-20 minutes from Knoxville and the famous Knoxville Raceway, making this an ideal spot for race fans. A short drive will also take you to Pella for the stunning Tulip Time Festival or to Des Moines for the iconic Iowa State Fair.
5.0 out of 5 average rating, 11 reviews
The Prayer Cabin
The Prayer Cabin is located at Lake Red Rock outside of Pella, IA. The cabin Is an Earthen/Berm home located on a 1 acre lot in a quiet & clean neighborhood. The lot boasts a wooded valley with many birds and squirrels to watch. The Prayer Cabin was recently remodeled with a brand new kitchen and bathroom. Our first guests asked us if Chip and Joanna were the creators of the design. 💚 Navy Blue cabinets, Tons of white shiplap and open shelving. Peaceful. A place of respite and relaxation.
4.96 out of 5 average rating, 184 reviews
8000sqft Barndo | Indoor Court + 2 Living Qtrs
Welcome to The Lodge on 3rd - a massive 8000 sq ft Barndominum. Nestled in the heart of Des Moines, Iowa, this stunning retreat offers the perfect blend of rustic charm and modern elegance. With 4 spacious bedrooms and a large loft, there is plenty of room for you and your guests to unwind in style. This property is next door to Luxury Living on Third. airbnb.com/h/luxurylivingonthird These combined properties are ideal for family reunions, etc. ***$200 Pet Fee***
5.0 out of 5 average rating, 175 reviews
Charming Home in Indianola
Discover comfort in our newly remodeled 3-bedroom home in the heart of Indianola, Iowa. This charming space boasts modern amenities and stylish decor, providing a cozy retreat for your stay. Enjoy a fully equipped kitchen, spacious living areas, and a modern bathroom. Perfect for families or groups, our home offers a blend of convenience and warmth. Explore nearby attractions or simply relax in our inviting space. Your home away from home awaits in Indianola!
4.93 out of 5 average rating, 212 reviews
Farmhouse-ish - all the charm without the farm
Tranquil Country Retreat on 2 Private Acres Escape the hustle and bustle at our peaceful rural getaway set on two acres with panoramic country views and star-filled skies. Enjoy morning coffee on the porch and unwind by the fire pit in the evenings. Our charming country home blends rustic charm with comfort — the ideal place to disconnect and recharge, while still being just 7 minutes from downtown Carlisle and 25 minutes from Des Moines.
5.0 out of 5 average rating, 17 reviews
New A-Frame Cabin by Des Moines (Hackberry theme)!
Escape to one of our three brand-new, fully furnished A-frame cabins at River Oaks RV Park—where modern comfort meets rustic charm. Each A-frame is uniquely designed, stylishly appointed, and perfect for making unforgettable memories. Whether you’re relaxing by the river, roasting s’mores under the stars, or just soaking in the cool, creative vibe of your private space, this family-friendly getaway is anything but ordinary.
5.0 out of 5 average rating, 17 reviewsPopular amenities for Pleasantville holiday rentals
Other great holiday rentals in Pleasantville

Vintage Downtown Loft
4.88 out of 5 average rating, 26 reviews
Convenient Townhome (3 Bdrm / 2.5 Bath)
4.96 out of 5 average rating, 57 reviews
Home w/ Pool/Hot Tub- Knoxville/Pella/DesMoines IA
5.0 out of 5 average rating, 13 reviews
Woodland Estate
4.96 out of 5 average rating, 25 reviews
Nice 3 bedroom ranch home w/ garage
5.0 out of 5 average rating, 33 reviews
Double E LLC Farm House
4.92 out of 5 average rating, 39 reviews
Sandstone Creek Barn
5.0 out of 5 average rating, 21 reviews
Farmhouse for Every Occasion
4.93 out of 5 average rating, 14 reviewsDestinations to explore
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